78386-74-0

Upstream product

• 124-41-4 sodium methylate 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 146137-80-6 2-fluoro-4-methylbenzaldehyde 
• 103-67-3 benzyl-methyl-amine 
• 67-68-5 dimethyl sulfoxide 
• 17485-25-5 3-methyl-N-nitroso-N-methylaniline 
• 673-32-5 1-Phenylprop-1-yne 
• 72233-91-1 1-methyl-1-m-tolylhydrazine 
• 108-44-1 1-amino-3-methylbenzene 
• 78386-75-1 1,3,4,6-Tetramethyl-2-phenyl-1H-indole 
• 68674-48-6 3,6-dimethyl-2-phenyl-1H-indole 

Downstream Products

• 78386-82-0 2-Methoxy-2,4,6-trimethyl-3-phenyl-3,4-dihydro-2H-benzo[1,4]oxazine 

Relevant academic research and scientific papers

Potassium tert-Butoxide-Mediated Condensation Cascade Reaction: Transition Metal-Free Synthesis of Multisubstituted Aryl Indoles and Benzofurans

An efficient and facile method to synthesize valuable disubstituted 2-aryl indoles and benzofurans in good yields has been demonstrated, based on a tert-butoxide-mediated condensation reaction involving a vinyl sulfoxide intermediate. Products are obtained from N- or O-benzyl benzaldehydes using dimethyl sulfoxide as a carbon source. The methodology features a wide functional group tolerance and transition metal-free environment. Preliminary mechanistic studies suggest that the reaction involves a tandem aldol reaction/Michael addition/dehydrosulfenylation/isomerization sequence through an ionic protocol.

Ruthenium(II)-Catalyzed Traceless C?H Functionalization Using an N?N Bond as an Internal Oxidant

A previously elusive RuII-catalyzed N?N bond-based traceless C?H functionalization strategy is reported. An N-amino (i.e., hydrazine) group is used for the directed C?H functionalization with either an alkyne or an alkene, affording an indole derivative or olefination product. The synthesis features a broad substrate scope, superior atom and step economy, as well as mild reaction conditions.

A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles

A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.

Rhodium(III)-catalyzed indole synthesis using N-N bond as an internal oxidant

We report herein a Rh(III)-catalyzed cyclization of N-nitrosoanilines with alkynes for streamlined synthesis of indoles. The synthetic protocol features a distinct internal oxidant, N-N bond, as a reactive handle for catalyst turnover, as well as a hitherto tantalizingly elusive intermolecular redox-neutral manifold, predicated upon C-H activation, for the formation of a five-membered azaheterocycle. The compatibility of seemingly dichotomous acidic and basic conditions ensures reaction versatility for multifarious synthetic contexts. The tolerance of an array of auxiliary functional groups potentially permits predefined, programmable substitution patterns to be incorporated into the indole scaffold. Comprehensive mechanistic studies, under acidic condition, support [RhCp*]2+ as generally the catalyst resting state (switchable to [RhCp*(OOCtBu)]+ under certain circumstance) and C-H activation as the turnover-limiting step. Given the variety of covalent linkages available for the nitroso group, this labile functionality is likely to be harnessed as a generic handle for strikingly diverse coupling reactions.

UNE NOUVELLE METHOXYLATION D'HYDROPEROXY-3 INDOLINES ISSUES DE LA PHOTO-OXYGENATION D'INDOLES EN MILIEU REDUCTEUR

3-Hydroperoxy-1,3,6-trimethyl-2-phenyl indolines coming from the senzitized photo-oxygenation of the indoles in presence of KBH4 rearrange partially in basic methanol into the corresponding 3-hydroxy-6-methoxymethylindolines.